Field of the Invention
The invention relates to the technical field of herbicides, especially that of herbicides for selective control of broad-leaved weeds and weed grasses in crops of useful plants.
Description of Related Art
WO1999/05130 A1 discloses herbicidally active 3-phenylisoxazolines substituted in the 5 position by a hydroxyl and trifluoromethyl group inter alia. WO2005/021516 A1, WO1995/014680 A1, WO 2008/035315 A1, WO2005/051931 A1 and WO2005/021515 A1 each describe, inter alia, 3-phenylisoxazoline-5-carboxylic acids, -carboxylic esters and -carbaldehydes substituted on the phenyl ring in the 3 and 4 positions by alkoxy radicals. These compounds are described as precursors for preparation of pharmacologically active 3-arylisoxazoline-5-carboxamides. J. Med. Chem. 42 (1999) 2760 described the compounds methyl 3-(3-cyanophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate, ethyl 3-(3-cyanophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate, 3-(3-cyanophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid and methyl 3-(3-cyanophenyl)-5-(methoxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate as pharmacologically active. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1993), 32B(9), 938-41 discloses the compound methyl 5-methyl-3-(3-nitrophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate. Izvestiya Akademii Nauk, Seriya Khimicheskaya (1996), (2), 426-429 mentions the compound methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate. Under the following CAS numbers, the compounds which follow each one are known:    1326815-55-7: 3-(3-bromophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326814-80-5: 3-(5-bromo-2-fluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326811-51-1: 3-(5-bromo-2-methoxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326813-57-3: 3-(3-bromo-4-methoxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326814-71-4: ethyl 3-(3-chlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate,    1326810-45-0: 3-(3,4-dichlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326815-81-9: 3-(2,5-dichlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326813-44-8: 3-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326810-59-6: 3-(2-chloro-5-nitrophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326814-16-7: 3-(3-chloro-4-fluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326815-03-5: 3-(3-fluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326810-73-4: 3-(3,4-difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326811-86-2: 3-(2,5-difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326811-50-0: 3-(2,3-difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326813-45-9: 3-(4-fluoro-3-methoxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326813-37-9: 3-[2-fluoro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326811-79-3: 3-(3-methoxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid    1326811-74-8: 3-(2,5-dimethoxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326814-78-1: 3-(3-methylphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid    1326813-55-1: 3-(2,5-dimethylphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326815-05-7: 5-methyl-3-(3-nitrophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1326812-83-2: 5-methyl-3-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole-5-carboxylic acid,    1027426-25-0: methyl 3-(3-cyanophenyl)-5-(ethoxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate,    1026410-22-9: methyl 3-(3-cyanophenyl)-5-(isopropoxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate,    1027205-06-6: methyl 5-(butoxymethyl)-3-(3-cyanophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate,    231300-28-0: methyl 3-(3-cyanophenyl)-5-(2-methoxyethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, and    1026948-50-4: 3-(3-cyanophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid.
No herbicidal effect of the compounds known by their CAS numbers has been disclosed.